Optically active epoxides provide useful building blocks in the synthesis of many biologically active compounds, and much research has been conducted on practical, efficient methods for the synthesis of such epoxides. For example, numerous catalysts have been developed to perform epoxidation reactions, in which an alkene is converted to an epoxide by addition of one oxygen atom to a carbon-carbon double bond. In particular, the “Shi Epoxidation,” is an enantioselective epoxidation method developed by Prof. Yian Shi and coworkers, which utilizes Shi catalyst 1, shown below.
While the Shi Epoxidation method has been shown to be effective for enantioselective epoxidation reactions, to date, Shi catalyst 1 can only be produced in large quantities as one enantiomer. The absence of the availability of the enantiomer of Shi catalyst 1 has hindered the more widespread use of the Shi Epoxidation.